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Sigma-Aldrich

Hypericin from Hypericum perforatum

~95% (HPLC)

Sinônimo(s):

4,5,7,4′,5′,7′-Hexahydroxy-2,2′-dimethylnaphthodianthrone, Cyclo werrol, Hypericum red

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About This Item

Fórmula empírica (Notação de Hill):
C30H16O8
Número CAS:
Peso molecular:
504.44
Beilstein:
1917913
Número CE:
Número MDL:
Código UNSPSC:
12352202
ID de substância PubChem:
NACRES:
NA.77

Ensaio

~95% (HPLC)

solubilidade

1 M NaOH: 10 mg/mL, turbid, dark green

cadeia de caracteres SMILES

Cc1cc(O)c2C(=O)c3c(O)cc(O)c4c5c(O)cc(O)c6C(=O)c7c(O)cc(C)c8c1c2c(c34)c(c78)c56

InChI

1S/C30H16O8/c1-7-3-9(31)19-23-15(7)16-8(2)4-10(32)20-24(16)28-26-18(12(34)6-14(36)22(26)30(20)38)17-11(33)5-13(35)21(29(19)37)25(17)27(23)28/h3-6,31-36H,1-2H3

chave InChI

BTXNYTINYBABQR-UHFFFAOYSA-N

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Descrição geral

Hypericin hydrophobic is a red color pigment occurring naturally in Hypericum perforatum. Its fluorescence is measured at 600 nm. It is localized in the intracellular membranes including nuclear membrane, mitochondrial membrane, Golgi apparatus, lysosomes and endoplasmic reticulum.

Aplicação

Hypericin from Hypericum perforatum has been used:
  • in the broth macrodilution test and antibacterial assay against bacterial strains
  • as a medium supplement for human malignant melanoma cells for irradiation and localization studies
  • as a ligand for pregnane X receptor (PXR) and as defatting medium supplement for primary human hepatocytes culture

Ações bioquímicas/fisiológicas

Hypericin is a potent inhibitor of protein kinase C (PKC), telomerase, cytochrome P450 and reverse transcriptase. It is exploited for its photosensitizing functionality in photodynamic therapy (PDT) and photodynamic diagnosis (PDD) in cancer cells.
Anthraquinone-derivative within St. John′s wort. Antibacterial effective against Gram-positive and Gram-negative bacteria.

Embalagem

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictogramas

Exclamation mark

Palavra indicadora

Warning

Frases de perigo

Declarações de precaução

Classificações de perigo

Acute Tox. 4 Oral

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves


Certificados de análise (COA)

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Antibacterial effect of hypericin
Feyziouglu B, et al.
African Journal of Microbiology Research, 7(11), 979-982 (2013)
I Lopez-Bazzocchi et al.
Photochemistry and photobiology, 54(1), 95-98 (1991-07-01)
The polycyclic compound hypericin, a known photodynamic agent, was investigated for antiviral activity in the presence and absence of light. The three viruses tested: murine cytomegalovirus; Sindbis virus; and human immunodeficiency virus type 1, were all susceptible to hypericin; but
Hypericin in the light and in the dark: two sides of the same coin
Jendvzelovska Z, et al.
Frontiers in Plant Science, 7, 560-560 (2016)
Susceptibility of In Vitro Melanoma Skin Cancer to Photoactivated Hypericin versus Aluminium (III) Phthalocyanine Chloride Tetrasulphonate
Ndhundhuma IM and Abrahamse H
BioMed Research International, 2017 (2017)
Noemí Rubio et al.
Autophagy, 8(9), 1312-1324 (2012-08-15)
Although reactive oxygen species (ROS) have been reported to evoke different autophagic pathways, how ROS or their secondary products modulate the selective clearance of oxidatively damaged organelles is less explored. To investigate the signaling role of ROS and the impact

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